13 Fall Events To Explore Around Central Oregon

Autumn in Central Oregon arrives with cool mornings, golden light through the pines and a variety of local events ready for discovery. From stargazing nights at the Sunriver Observatory to music festivals in Sisters, family-friendly art shows in Bend and Oktoberfest celebrations in Sunriver, the season offers endless opportunities to connect with the community, experience local culture and enjoy the landscapes that define the region.

Here’s a look at what’s ahead in the surrounding area of Caldera Springs this fall:

In-Depth Observatory Nighttime Visit

September 10, 2025 • Sunriver, OR

Seek the stars at the nation’s largest collection of publicly accessible telescopes at the Sunriver Nature Center & Observatory. These two-hour sessions begin with an educational presentation, followed by telescope viewing guided by staff astronomers and a constellation tour. Offered on select Wednesdays and Saturdays throughout September, the program runs regardless of weather, with activities adjusted as needed. Advance tickets are required, and capacity is limited, making it a memorable way to experience the night sky just minutes from Caldera Springs.

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Cascade Equinox Festival

September 19–21, 2025 • Redmond, OR 

The Cascade Equinox Festival returns for its third year, marking the autumnal equinox with three days of music, art and immersive experiences in Central Oregon’s high desert. The festival pairs a diverse lineup of musical acts with visual and performance art, interactive installations and workshops ranging from movement and healing to flow arts and music. Families will find kid-friendly activities, while foodies can enjoy curated selections from local wineries, breweries and eateries. With camping options and an artisan market showcasing nomadic and handcrafted goods, Cascade Equinox is a celebration of creativity set against a stunning desert backdrop.

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Oregon Whiskey Festival

September 19–20, 2025 • Bend, OR

Whiskey lovers will gather at Oregon Spirit Distillers for a two-day celebration dedicated to spirits crafted entirely in Oregon. Featuring more than 20 participating distilleries—including names like Ransom Spirits, McMenamins and Crater Lake Spirits—the festival highlights whiskeys mashed, fermented, distilled and aged in-state. Guests can explore tastings, meet the makers and learn about the art of distilling. VIP experiences begin Friday evening with cocktails, live music, gourmet food and distillery tours, continuing into Saturday with early access to the main festival and special amenities.

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Sunriver Oktoberfest

September 26–27, 2025 • Sunriver, OR

This new Sunriver tradition in the Village  kicks off Friday evening with activities like a pig-themed “Freshies and Festies” beer showcase, bratwurst pop‑ups and an accordion performance. Saturday brings family fun with a market, fun runs (5K/10K/1-mile), live music, German-inspired food and beverages, costume and stein-holding contests, and more—creating a full weekend of Bavarian-themed enjoyment.

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Sisters Folk Festival

September 26–28, 2025 • Sisters, OR

Known as the festival where “All the Town’s a Stage,” the Sisters Folk Festival is an immersive celebration of music. For three days, seven venues across Sisters—including tents, a historic church, and local courtyards—welcome world-class musicians alongside emerging artists and songwriters. Since 1995, the festival has fostered a listening atmosphere that feels both intimate and transformative, offering unforgettable live performances in a picturesque mountain town setting.

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Fresh Hops on the Pond

October 3, 2023 • Bend, OR

Set along the water at Bend Brewing Company, this daylong celebration showcases the best of Oregon’s fresh hop beer season. More than 20 breweries will pour their latest releases, with live music adding to the festive outdoor atmosphere on the lawn and patio. Running from morning into evening, the event is open to all ages—and even pets—making it a family-friendly way to experience one of Central Oregon’s favorite fall traditions.

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The 20-Dollar Art Show

October 4–20, 2025 • Bend, OR

Bend’s biggest little art show returns, bringing nearly 10,000 original works by local and emerging artists to the High Desert Museum. Presented by the Bright Place Gallery, the exhibition opens October 4 and runs through October 20, with artwork available for purchase during the show’s signature Extravaganza weekend, October 17–19. The kickoff evening features a no-host bar, followed by morning sales on Saturday and Sunday. Affordable, community-driven, and always full of surprises, the 20-Dollar Art Show has become one of Central Oregon’s most anticipated annual arts events.

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Sunriver Resort Fall Festival

October 11–12, 2025 • Sunriver, OR

Sunriver Resort’s Fall Festival brings the season to life with a weekend full of activities for all ages. Families can enjoy pony rides, a petting zoo, a bounce house, face painting, and a festive pumpkin patch. Seasonal food and drink specials will be available at the Backyard Café and Bar, making it easy to spend the day soaking up the autumn atmosphere. The event is complimentary and open to the public—no tickets required.

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Bend Fall Festival

October 8–12, 2025 • Bend, OR

Downtown Bend, only 15 minutes from Caldera Springs, transforms into a harvest celebration during the Bend Fall Festival. Over 80 artisans and craftspeople showcase fine art and handmade goods, while Art in Action Avenue brings creativity to life with live demonstrations from blacksmiths, printmakers, sculptors, and more. Interactive installations add to the experience, alongside live music on multiple stages. Between browsing, enjoy local food and drink offerings, sip and shop through the festival streets, and soak up the energy of this annual autumn tradition.

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Bend Film Festival

October 8–12, 2025 • Bend, OR

Founded in 2003, BendFilm has grown into one of MovieMaker Magazine’s “Coolest Festivals in the World,” celebrating the power of independent cinema to inspire change, amplify diverse voices and educate future storytellers. The annual Bend Film Festival is its signature event, drawing more than 3,000 attendees for five days of screenings, panels and post-film conversations with visiting filmmakers and jurors. With over 130 films ranging from student projects to award-winning features, plus a focus on elevating women and BIPOC filmmakers, the festival has become a cornerstone of Central Oregon’s cultural calendar.

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Movies in the Mountains

October 17 & 24, 2025 • Mt. Bachelor, Bend, OR

Mt. Bachelor turns into a classic drive-in this fall with a screening of The Nightmare Before Christmas and Hocus Pocus under the stars. Guests can tune in from their car radios or bring a portable FM radio to enjoy the film from lawn chairs and blankets outside their vehicles. Concessions will be available on-site, making it easy to settle in for a cozy evening surrounded by Central Oregon’s alpine landscape. 

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Hearth Festival

October 18, 2025 • Sisters, OR

A daylong, hands-on celebration of the arts, this free, all-ages gathering at Caldera Arts in Sisters invites the community to explore art, music, film, food and play in a natural setting. Interactive maker stations encourage engagement with different mediums, while artisan foods and live performances add to the experience. With opportunities for both kids and adults to discover and create, Hearth Festival has become an inspiring autumn tradition that highlights the spirit of  imagination.

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Halloween in the Old Mill District

October 31, 2025 • Bend, OR

A free, family-friendly tradition in Bend, the Old Mill District Halloween celebration invites kids of all ages to trick-or-treat at shops and restaurants throughout the afternoon and early evening. Costumes are encouraged for the whole family, and participating businesses hand out candy in a safe and festive setting along the scenic riverfront.

Central Oregon offers endless opportunities to gather, explore and celebrate. At Caldera Springs, you’re not only surrounded by trails, lakes and year-round amenities—you’re also within easy reach of the festivals, concerts and seasonal traditions that make this region so vibrant. With new homes and homesites now available, ownership at Caldera Springs places you at the center of it all, giving you a front-row seat to both the natural beauty and the cultural richness of Central Oregon.

To learn more, contact our Sales Team at 541-593-3000 or sales@calderasprings.com.